2-[(2S,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-1(17),6-dien-14-yl]-2-oxoethyl acetate

• ChemBase ID: 125862
• Molecular Formular: C23H30O5
• Molecular Mass: 386.4813
• Monoisotopic Mass: 386.20932406
• SMILES: O=C(OCC(=O)[C@@]1(O)CC[C@H]2[C@H]3C(=CC[C@]12C)[C@@]1(C(=CC(=O)CC1)CC3)C)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC=C1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C23H30O5/c1-14(24)28-13-20(26)23(27)11-8-19-17-5-4-15-12-16(25)6-9-21(15,2)18(17)7-10-22(19,23)3/h7,12,17,19,27H,4-6,8-11,13H2,1-3H3/t17-,19+,21+,22+,23+/m1/s1
• InChIKey: YUWPMEXLKGOSBF-GACAOOTBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(17),6-dien-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: anecortave
• Synonyms: 21-(Acetyloxy)-17-hydroxypregna-4,9(11)-diene-3,20-dione; 17,21-Dihydroxypregna-4,9(11)-diene-3,20-dione 21-Acetate; 21-Acetoxypregna-4,9(11)-dien-17α-ol-3,20-dione; Al 3789; Anecortave; NSC 15475; NSC 24345; Retaane; Anecortave Acetate; Anecortave

Database IDs

• CAS Number: 7753-60-8
• PubChem SID: 162220207
• PubChem CID: 111332
• ATC CODE: S01LA02
• Chemspider ID: 99892
• Unique Ingredient Identifier: Y0PC411K4T
• Wikipedia Title: Anecortave

CALCULATED PROPERTIES

• Acid pKa: 12.606714
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.619477
• LogD (pH = 7.4): 2.6194744
• Log P: 2.6194773
• Molar Refractivity: 105.809 cm^3
• Polarizability: 41.239056 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid
• Melting Point: 230-234°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Admin Routes: intravitreal depot injection
• Legal Status: Schedule 4 (Aust)

DETAILS

Toronto Research Chemicals - A637640

Angiostatic steroid. Used in treatment of macular degeneration.

REFERENCES

• Clark, A.F., et al.: Expert Opin. Invest. Drugs, 6, 1867 (1997)
• Slakter, J.S., et al.: Ophthalmology 110, 2372 (1997)